Benzene, 1-bromo-3-(trifluoromethyl)- → 2,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-ol

HRID 614746Notes

Reaction equation

HRID 614746 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:13][C:14]1([CH3:26])[CH2:23][C:22](=O)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1.[Cl-].[NH4+]>CCOCC>[CH3:13][C:14]1([CH3:26])[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1

Participants

6

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

Product 1

HCID 120717572,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-olYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

3-Bromobenzotrifluoride (61 g) in dry ether (100 ml) was added to magnesium (6.6 g) in ether (50 ml). 2,2-Dimethylchroman-4-one-7-ol (17.4 g) suspended in ether (500 ml) was added and the mixture refluxed for 16 hours. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The combined ether layers were washed with 2N HCl (2 × 100 ml) and dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound (25 g), m.p. 102°-106° C.

Workup

  1. additionwas added
  2. temperaturethe mixture refluxed for 16 hours
  3. extractionextracted with ether
  4. washThe combined ether layers were washed with 2N HCl (2 × 100 ml)
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e8c5bb0ba11c45999c424ccbe996ed19
Source dataset
uspto-grants-1979_03
Patent number
US04146539

Reaction notes

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